Benzyl Bromide → 4-(benzyloxy)-N-phenylaniline

HRID 515895Notes

Reaction equation

HRID 515895 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([O:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 312084-Hydroxydiphenylamine

Product 1

HCID 2960794-(benzyloxy)-N-phenylaniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-hydroxy-N-phenyl-aniline (30 g; 162 mmol) in acetonitrile (400 mL) there are added 58 g of Cs2CO3 (178 mmol) and stirring is carried out for 15 minutes at ambient temperature. Benzyl bromide (22.5 mL; 178 mmol) is then added dropwise and then the reaction mixture is refluxed for 4 hours. After filtering and rinsing with acetonitrile, the filtrate is concentrated and purified by chromatography over silica gel using petroleum ether and ethyl acetate as eluants. The title product is then obtained in the form of a colourless solid.

Workup

  1. temperaturethe reaction mixture is refluxed for 4 hours
  2. filtrationAfter filtering
  3. washrinsing with acetonitrile
  4. concentrationthe filtrate is concentrated
  5. custompurified by chromatography over silica gel

Sources & evidence

ORD record
ord-e33c16b7ac2b48169432ff3da3fed603
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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